


Loyalty to the Evil Queen: Ainsley

by LMPsisterhood



Series: Loyalty to the Evil Queen [3]
Category: Once Upon a Time (TV)
Genre: Bondage, Chains, Cock Rings, Cunnilingus, Doggy Style, Explicit Sexual Content, F/M, Felatio, First Time, G-spot pleasure, Kissing, Nyctophobia, Oral Sex, Prostate Massage, Regina Mills is a screamer, Riding, Sex, Sexual Content, Spanking, Woman on Top, trigger warning: Bondage
Language: English
Status: In-Progress
Published: 2017-09-04
Updated: 2017-09-17
Packaged: 2018-12-23 22:49:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 9,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11999547
Author URL: https://archiveofourown.org/users/LMPsisterhood/pseuds/LMPsisterhood
Summary: Ainsley is just a boy, but Regina can't help reminiscing looking at his smoky blues. She decides she needs a new night guard. She could have some fun with this one - her precious boy toy!





	1. Chapter 1

**Author's Note:**

> This part of the story will see eight parts as I realized there was just so much to cover. I will try to publish as I finish each chapter and post trigger warnings when needed, please watch for them.

**In the Enchanted Forest: Ainsley**

**Chapter 1 The Queen**

Her majesty is so incredible and I’m so proud to be her personal guard. What she did to the hunter is infamous, but being here as her boy toy is one of my favourite things in the world. I remember the night when she had us take the hunter back to her chambers and we dragged him away. He only struggled a little bit; after all, she did take his heart. That was one thing she never did with us; she always wanted us to feel everything. And, boy, did we! I would never be disloyal to her. I **could** never be disloyal to her; she taught me how to be a man.

Anyways, I’m getting ahead of myself. She had just demoted another guard, when she brought me in. Heh, heh, heh, demoted is a term us guards like to use for when she takes a heart and puts them in the front line of her rank of soldiers. Unlike Oskar, who told us his story, I knew why I was brought in. I always did have a pretty face and she just couldn’t resist. I never thought I could ever catch the attention of the Queen herself. Did you catch that? To us, she’s not evil.

Queen Regina is the most incredible woman to have ever graced the face of all the realms. She treats us well and gives us everything we could ever need. We night guards make sure to give her all that she needs as well. I think I get the best of it though.

When I first came to her, I was still a youth, and like I just said, she made me a man. I was apprenticing to be a blacksmith when she found me. Even though I ignored the fawning, I knew a trail of girls followed me around making eyes at me. I was waiting for the right girl; one that would I could truly spoil and devote my time and energy on that would want true intimacy with me, not just my brawn. When her chocolate brown eyes rested on my smoky blues, I recognized the look as nostalgic. I knew she must have been thinking of something from long ago. Her and her soldiers moved away and continued on down the road. A moment later, one of her black knights stepped up to me and asked me to join their party at the queen’s request. At first, I was going to decline, but when I heard that the queen had asked for my presence, I knew it would be foolish to say no. After all, it could mean my life.

I asked the guard if he could give me the day, I just needed to find my employer and tell him of the circumstances. The guard started to protest, but I assured him I could be at the castle by no later than 7:00 pm, just a couple hours hence. I knew exactly where to find him and then I would say goodbye to my family, letting them know I would be servicing the queen. The soldier nodded at me as he understood that I knew what was going to happen to me once I got to the castle. The queen is not one to argue with. If she is not pleased, one’s life is forfeit.

The soldier joined his battalion again and I watched him go. The Queen twisted in her saddle to look at me with a curiously angry expression on her face. My heart pounded within my chest as I made my way down the street to find my master at his home with his wife. Just as I made it to his door, he stepped out and asked me what the commotion was and I told him about the Queen and her proposition. He patted me on the back and shoved me in the direction of the battalion. He was afraid for my life and wanted me to go right now before the Queen returned and took more lives than those of my family. I laughed at him, telling him everything was going to be alright.

Walking quickly to my family home, just a street over, I was home in 20 minutes. My mother was out in the back garden doing some laundry. While I helped her hang some linen on the line, I told her what had happened at the blacksmith’s shop as the Queen passed by. She yelped and burst out crying, throwing her arms around my neck and soaking through my shirt. I patted her back to calm her, but she scrambled out of my arms and rushed into the house. She quickly put my things together and dipped into the family’s coin jar, passing me a crown. She told me to get something pretty for the Queen to apologize for not coming sooner. Even though I didn’t deem it necessary to take from my family, I thought she had a point and told her I would pay her back, if the Queen ever paid me.

My mother shook her head and scolded me. She didn’t want me to worry about the family. I was now in the Queen’s service and my responsibilities were to tend to my job, all our lives were at stake if I didn’t. I gave my mother another hug and kiss before I hurriedly ran to market before it closed. I found this beautiful amethyst broach in the shape of a feather and purchased it for my new employer. Taking all I had with me, I strode with purpose to the Dark Castle and her Royal Majesty, not realizing what kind of service was required of me, but all the more willing for it.

* * *

I was taken directly to the Queen. The guard outside her office chuckled slightly as he let me pass, giving me a once over. His brow rose as he gave a nod of agreement. A quizzical look passed over my face as I walked into a rather large office with magnificent furniture. The queen had taste and I appreciated the art work on the walls as I waited for her majesty to acknowledge me.

She turned on her seat and at first she looked shocked, but it quickly changed to a pleased expression and then into a more passive expression. I smiled as she gave me a once over, following her eye line up from my toned legs and thighs, narrow waist, firm chest, strong muscled arms and thick neck. As I looked over her busty chest, curvaceous figure and fine facial features, I felt her eyes on me as she studied my thick eyebrows, broad forehead, straight nose, chestnut brown hair, square jawline, full bottom lip and then finally making eye contact and staring straight into my smoky blue eyes. I loved her beautiful chocolate eyes studying my features.

She finally spoke, and I listened enraptured to her sexy, sultry voice, “What is your name?”

“Ainsley Ward, your majesty,” I replied in a monotone voice. She pursed her full lips and both eyebrows rose. Her small smile fell flat.

Queen Regina stood and walked toward me, her hand took on an exotic look as she trailed her middle finger over my chest. My eyes widened as I watched as the finger trailed down my chest. She grinned evilly at me and asked, “Have you ever been with a woman?”

“No, your majesty,” I picked a spot on the floor to stare at as I felt my cheeks flush. “I have one more year to become a journeyman and I was waiting to pick one of the fairer sex for myself when I knew I could better provide for her and our family.”

The Queen’s nostrils flared and she visually gulped as she said, “Maybe one day I will let you go so you may choose a mate, but until that time, would you like to properly learn how to please one?”

I gulped and felt my Adam’s apple bob as I stared at this beautiful woman and learning the fine art of seduction and intercourse from her. Would I ever really want to find a mate? Would she ruin me to ever want to leave her presence ever again? Would I lose my heart to her? In just above a whisper, I replied in the only answer that would please her, “Yes, your majesty.”

A momentary look of concern passed over the queen’s face before she asked, “What is your age?”

“I am now in my seventeenth year as my sixteenth year completed during the full moon of the fourth month.” I honestly answered. Even though it wouldn’t matter the age of a boy if the queen really wanted them, I knew my age would please her better as I was old enough to consent and young enough to learn. I was right as a pleased look passed over her beautiful face.

“Follow me,” she commanded as she walked towards the door, “we will begin right away.” Opening it, she walked out into the corridor and told the guard there, “I will take dinner in my rooms. Make sure there is enough for two as what I have to teach my new personal guard he will require sustenance and strength.”

The guard smirked as he turned to find his way to the kitchens. I nervously, but happily, followed my queen as she guided me towards her rooms.

As this was my first-time walking into her rooms, I took a moment to look them over. Definitely fit for a queen, but lacking in femininity, except her bed. The bed had black silk bed clothes with a slight frill on the decorative red pillows gracing the bed. Her dressing table held her cosmetics, brushes, combs, pins and hair bobbles, showing that indeed a woman did live here. Having grown up with two older sisters and three younger, I was used to these things that a woman uses to dress herself up. My eldest two brothers were grateful when they finally wed and started their own families to get away from six women, including our mother. I laughed silently to myself, thinking about Addison and the fact that he already had three daughters of his own, waiting for his first-born son to make entrance. Looking at the queen’s dressing table though, I missed my family and the chatter that would be going on around the dinner table right now and I sighed noisily.

The queen looked up at me and trailed a hand up my arm, pursing her lips as she stared deeply into my eyes. I watched her as she thought silently and wondered what she was pondering so deeply. So few of the villagers really knew her story and I had a feeling that she was remembering something as she didn’t stray from looking directly into my smoky blues.

The doors opened and the queen started, turning away from me and I sighed once again. That moment when we held each other’s gaze, I felt a slow curl of arousal deep in my belly and my member stirring, but with the entrance of the kitchen servant the moment was lost and I happily left the arousal alone for just the right moment. The queen gestured to the chair across from her and I strode the few steps to sit for dinner.

The servant lifted the dome from the dinner tray and revealed a nice plate of trout with rice and the season’s best vegetables. I sat across from the Queen keeping my head down, giving respect to my Queen. I looked up through my low bangs and she smiled slightly at me. I ducked my head a little more. As dinner finished, the Queen sat and wiped daintily at her mouth. I admired the fullness of her lips and was taken in by her scar. I set down my utensils and used my napkin to show my manners.

Queen Regina slowly turned in her seat and came to standing. She looked directly into my eyes and remarked, “You agreed to this; don’t forget that now.” She turned on her heel and walked the few steps to a door in her bedroom that appeared as she stood in front of it. “Follow me.”

I quickly walked up behind her so as not to get too far behind and followed her through the door and down a set of stairs into the darkness. Fear squeezed at my heart. I never liked the dark, probably because of the vicious prank my second oldest brother, Roderick, pulled on me when I was but a lad during Halloween. When we came to the ground floor, Queen Regina scooped a fireball from within her and blew it into the room. The fire separated and ignited each torch in the room giving a warm blaze to set the atmosphere. Lastly, she pulled out another fireball and sent it into the fire grate. I looked at her in awe – such power. I knew I was in the presence of greatness.

She stood regally and gestured at the room. I allowed my eyes to gaze at the room around me. There was a bed against the wall, each post had chains hanging from it. The bedding was black silk. As my eyes continued to wander, I saw a shelf that had a variety of paddles on it. There were chains hanging from the walls and ceiling. In one corner, I saw a swing. I wondered how that was used and what kind of pleasure that could bring. Another shelf held many different types of instruments shaped in nothing else than what could be considered a penis. I shuddered to think that she would use those on me. Maybe she would allow me to use those on her. I would just have to wait and see.

Finally, my eyes rested on my Queen and I lowered my head in abeyance. Queen Regina rested her left hand in my right and led me to sit on the bed, at which point she swirled away our clothes. Boy, I wished right then I could study the nakedness of this beautiful woman, but I still had my eyes lowered and she had not given me permission to look up yet.

There was a clink against the floor and I looked down. I had forgotten the feather broach. The glitter of the gems caught the Queen’s eye and she stooped down to pick it up. “How lovely,” she murmured as she fingered over the jewelry. She looked up into my eyes and asked, “Is this for me?”

A single finger reached forward to tip my chin up and I gazed into the chocolate eyes of my Queen. It was then that I nodded my reply. The finger traced its way down my chest over my abdomen and then down my semi-flaccid cock. Her fingers then circled around my member and squeezed lightly.

“Thank you, Ainsley. It’s beautiful. I will treasure it.” It poofed from her hand and I supposed it now graced her dressing table. Who knows what she really did with gifts from her admirers? She continued to hold my gaze and then she lowered herself to her knees. She opened her mouth and her tongue touched my tip. I watched as she enveloped my cock in her mouth.

            My eyes closed and I felt her fingers squeeze my balls and they flew open again. I caught her gaze again as she twirled her tongue over and around. She lip bit her way down my cock and she held my gaze the whole way. I gulped. How sexy was she? My shaft got harder as she slid off to my tip and almost swallowed my cock whole again. As she continued to pump, her tongue ever swirled around my cock. My balls got tight and I wanted to scream for her to stop; I didn’t want to come in her mouth, but I couldn’t. She was just so hot! She fondled my balls as she moved over my cock. My tummy tightened with my balls and too quickly I released in her mouth.

Much to my surprise, she swallowed my seed and licked her lips afterward. My heart swelled beyond its capacity. This woman was so sexy. I knew she would take my heart, just not this way. Please, please, please, my Queen, don’t ever crush it. I’m yours for always. Should I say this out loud? Would she be pleased?

She picked herself from her knees to stand before me. I felt ashamed that I had cum so quickly. I was pretty sure my cheeks were pinked with my shame and I hung my head before my Queen.

She tilted my head up and I averted my eyes from looking straight in her chocolate browns. “Ainsley, my dear, do not be ashamed. This is your first time. Of course you would cum quickly. I made sure you would, hoping that we have a bit of time before your second.”

I looked up as she stepped away from me and draped herself at the head of the bed. Her eyes lowered and my breath caught at her sultriness. “Come to me, my sweet.”

Slowly I crawled up the bed and, in deference to my Queen, I lay my head against her shoulder. She looked down on me and smiled. She stroked her hand over my cheek and entangled her fingers in my hair. Her cheek rubbed mine and her lips moved over mine and captured them. Her tongue darted out every once in a while, until finally I captured the tip in my mouth and sucked at it. Her breath caught and she moaned into my mouth.

I moved from her mouth over her jawline and down her throat. Her throaty moans encouraged me to continue. I sucked lightly over her pulse point but didn’t linger. Lightly nipping and kissing, I kissed over her collar bone and over the softness of those perfect spheres, taking a dusky nipple into my mouth. I remembered her swirling her tongue over my cock and thought I would try that over her nipple. She mewled as I swirled and then I scraped my teeth over it and she pressed my head into her breast. I sucked lightly and her moans turned to whimpers. I wrested my head out of her fingers and kissed my way over to her other to pay it the same attention.

Out of the corner of my eye, I saw how she fingered the nipple I left behind and I knocked her hand aside so I could finger over it while I sucked at the left one. She thrust her chest up into my willing hand and mouth, moaning deep in her throat. A couple minutes later, her hands pushed my head away from her breast directing me down. I licked at her skin, alternating between licking and kissing, I moved my way over her tummy and down into what my brothers used to label ‘no-man’s-land’ when we were just but children and what I knew now as a woman’s vagina.

She had a small triangle of hair pointing the way down into her precious oyster. I pulled lightly at the hair and she bucked. I kissed over her nether lips. I really was in no-man’s-land because I wasn’t sure what to do. I popped my head up to take a look and figure out the best course of action. I heard her chuckle and looked up into her lovely face.

“I keep forgetting this is your first time. You’re doing so well.” She smiled at me and I smiled back. She enjoyed what I was doing to her. I felt good. Her right hand moved in between my head and her oyster and she pulled the lips apart and my mouth fell open in awe. Women were so much more beautiful than men! My chest swelled as I inhaled and dove right in.

She bucked again as my tongue touched her inner folds. My nose bucked against her nub. Her pearl, that’s what I would nickname it as I considered her vagina her oyster. She moaned as my nose knocked against her pearl again. It looked as spongy as my member and she liked when I touched it. I touched her pearl with my tongue and sucked it into my mouth. She mewled again and I knew I had done something right. I kept a nice suction in my mouth, touching the head of her pearl and her thighs quivered around my head. I wanted to discover more about her oyster and searched with my fingers through her folds. She pushed her folds against my finger again and again. My index and middle fingers slid through her wetness and found a depth that needed further discovering.

I dove my fingers through her walls and yet again she bucked against me. They were so soft and I couldn’t get enough of touching them. I twisted and twirled them about inside her, walking them against her belly side. My index found a corrugated area and I heard her whisper ‘yes’ above my head. I pushed both fingers against this area and her body thrust against my fingers.

“Yes, yes, yes,” Queen Regina chanted with each yes getting louder. Finding her rhythm, I thrust my fingers against this spot. Her chant kept getting louder until she was practically screaming it. Her walls undulated around my fingers and her butt lifted off the bed. The Queen’s vocal cords opened up and she screamed as her body shook through her high. I pulled back to watch as she fell back to the bed, still moving my fingers inside her.

My cock was throbbing watching her in the throes of passion and a moment later I felt her hand grasp my shaft and tug. What did she want? She was directing me towards her grasping hole. I got the message and pushed forward; feeling for the first time a woman’s vagina enveloping my penis. But I didn’t have time to relish it as she pulled my shoulders over her. Her arms hooked under my pits and she pushed her pelvis up, rolling me over. She pulled herself off me and then quickly dropped again, impaling herself on my cock once again.

Impaling herself again and again, I watched her breasts bounce in my face as her hands rested on my chest. “Oh, oh, oh,” she started to chant. She had never quite finished the last one and I thought maybe she climbing even higher. The look on her face looked of pure bliss. Her vocalizations gave me pure happiness and I smiled as she continued, “Oh yes, oh yes, oh yes. Yes, yes, yes!”

Her walls fluttered around my cock and I couldn’t hold it anymore. I released inside her tight walls, light exploding in my eyes. Spots swam in my vision as it came into focus. I looked up into her chocolate browns as she caressed over my face. Her lips lowered over mine and yet again she captured my lips; her tongue opening my mouth, swirling over my tongue and then brushing over the roof. As her tongue slipped out, she caught my upper lip between hers and gave a hard suck. A few pulses later she released it and I ran my tongue over my engorged lip and smiled at her.

“Thank you, Ainsley. You learn fast, my dear.” She picked herself off my limp cock and as she stepped to the floor, her clothes swirled back on. “Tomorrow we’ll go over the rules and continue where we left off, my sweet.”

She gave me a coy grin and I smiled at her cheekiness. I made to get up from the bed, but then I felt the chains snake around my wrists and the binders lock me in place. She swirled a loincloth around my hips. “Your majesty,” I timidly called to her as she ascended the stairs, “what if I need to …”

She turned to look at me at the last second and told me, “There is a chamber pot beside the bed. Your chains are enchanted; they will move with you, but you will not be allowed to leave this chamber. See you in the morning, sweet dreams.”

As the door closed behind her, the lights turned out and I was left in the utter darkness. No windows to let in the moonlight and my heart pounded within me. I wanted to cry.


	2. Day 1

**Summary for the Chapter:**

> Queen Regina takes the time to lay out the rules for Ainsley. Ainsley in curiosity asks how she attained her instruments. Regina tells him a story. Ainsley is punished for the first time. Trigger Warning: spanking.

**Chapter 2 Day 1**

Ainsley spent most of the night in a cold sweat. The hoot of an owl frightened him at first, but it was all the little sounds he didn’t know that scared him the most. After hours with terror squeezing his heart, he finally fell into a restless sleep. He was startled awake by the scraping of the door opening. The lights went on and before his Queen made an appearance, he quickly used the chamber pot.

He scrambled back on the bed as the Queen slowly made her way down the stairs. He gulped. Regina wore a black leather corset that showed off her cleavage. Her leather panties revealed the little triangle pointing the way to her pussy. Were they … crouch less? She was wearing a sheer skirt over her buttocks but not in the front, showing off her beautiful toned legs. Her hair was up with curls around her face and trailing down her back. She held a cat o’nine tails in her hand. In a loud whisper, she said, “Good morning, Ainsley.”

“Good morning, your Majesty.” My stomach muscles crunched as I pulled myself to a sitting position. I pulled my hand over my stubbled jawline.

“Would you like a shave?” She sat down beside me and ran her hand over my jaw. “Although it might be nice to have a clean-shaven face eating me out, I’ve always liked a little hair on a man’s face. What do you think?”

“I want to please you, your majesty. What do you wish?” She pulled my face towards hers and captured my lips. I ran my tongue against her crease and her tongue darted out to dual with mine before she kissed me hard and then pulled away, still holding my head in her hands. My breath was heavy as I stared deeply into my Queen’s eyes.

“Very good, my sweet, you have learned well in such a short amount of time.” Her hand caressed over my chest and came to rest on the mattress between my legs as she studied my face. “Now, before we begin, would you like something to eat?”

She swirled her hand and a tray was heavy on my legs. There was a plate full of eggs, sausage, fried potatoes, half a tomato and some mushrooms. There was a mug of ale on the tray which made it extraordinarily heavy. “Uh,” she looked at me expectantly, “I’m sure most of your guards drink ale first thing in the morning, and maybe I’ll learn to drink that too, but I would much rather some tea.”

She swirled her hand over the tray and the ale disappeared. A tea cup and kettle took its place and I fixed myself a cup of black tea with one sugar. Taking a sip of the tea first, I dug into my plate of food. I hoped the kitchen staff had cooked this and Queen Regina hadn’t whipped it up. Did she even know how to cook? She was a queen, probably not. I groaned at the deliciousness of the food, and took another sip before I devoured the rest of it. Once breakfast was done, I sipped at my tea and watched my queen as she went over her inventory of paddles.

Once my tea was finished and I had finally set the cup on the saucer, she turned towards me and magicked the tray away. She gave me a sultry look as she walked to me and smiled as she gently scratched my chest. She pulled at the tuffs of hair on my chest and a smile played over her face. Obviously, I hadn’t quite grown into a man yet as I wasn’t covered in hair yet. I always figured though, that a man was not defined by what he looked like, but how he treated those he values, keeping his promises and protecting those he loves. All these things I intended to do for this incredible woman before me for as long as she let me, and maybe one day, I’d tell her.

“Alright, last night was a one-time event. I wanted to take your virginity a little more gently than what I have in store for you in the future.” She spun on her heal and raised her hands up to shoulder level and turned out to the high ceiling. She had a wide smile on her face as she said, “Welcome to my playroom. I affectionately call it my sexual torture chamber, but it won’t be painful unless you disobey me. I created it for pleasure, of which, I’m going to teach you everything.”

She graced her body over the foot of the bed, so that I could see everything. She held my gaze and continued with her teaching, “Once I enter this room, you will address me as Mistress and whenever answering any questions you will address me properly. You will not speak out of turn or raise your voice, only with the exception of your safe word. Do you know what a safe word is?”   

I looked down in deference to my Queen and pondered. I had an inkling, but I wasn’t sure, so I said, “No, Mistress.”

She smiled at the use of the term and reached out to tip my chin up. “Ainsley, I am pleased with you and you need not look down when I’m talking. I expect you to look at me all the time.” My eyes shone as I looked into her eyes. “You are my special one. I’m going to teach you all I know and then we’ll learn together. A safe word is a word you choose that you use when you can’t handle the teasing or pain anymore. I’m going to tell you, pain will only happen when you disobey.”

“Yes, Mistress.” I agreed with her. This sounded interesting. I had heard about people that were kinky like this, but it wouldn’t hurt to try. I might even enjoy it, for all I knew.

She looked at me with kindly eyes, saying, “You look so curious and I’m glad. Just because I have all the control here, doesn’t mean I have all the power. This is for your pleasure as much as mine and you hold the power to tell me what works for you. Now, let’s go over some of the rules. Number one, your orgasms are mine. You will not have one without permission. I will punish you if you don’t do as you are told. Number two, use your words. I don’t want anything getting lost in translation because you wouldn’t say what you meant. Don’t be afraid to use your safe word.

“During our afternoon sessions and after this week when I let you down in this room, you will come kneel on this stool with your hands behind your head. Come here.” I stood up from the bed and made my way to the stool about five feet away from the foot of the stairs. “So, this is number three. You will face the bed and look straight ahead. Unless I give you a command, you will look straight ahead at all times. Number four, you will remember a set of commands and obey them without question. If you don’t, you will be punished. Number five, punishment is up to my discretion. Punishment includes and is not limited to spanking, flogging, standing in a corner, withholding orgasms, etc.

“Number six, now this is important, if you reach your limit and you need to stop, I need you to use your safe word or I will keep going with whatever I have planned. Understood?” She reached out and ran her hand over my jawline. She frowned and caressed her cheek over mine. “You know what, I think you’re right. I’m going to need you to bathe.”

She walked to the middle of the room and looked around. She walked over to the corner and removed the wooden stool. She swirled her hand and a tub appeared with hot water in it. A small mirror appeared on the wall with a stand and bowl. A razor appeared beside it with a small brush and cream cup.

“May I approach, Mistress?” I still had my hands behind my head, kneeling.

She smiled at me. “Yes, you may.” I stood and walked over to the corner to take care of my toiletries. “I’m going to step out momentarily. When you are done, please resume you’re position and I will know to come back down.”

Before she left, she put a spell on the stool. Nervously, I watched the stool wondering what it would do. I caught myself and turned back to my task at hand. I didn’t want to take too long and waste my Queen’s time. I’m sure she had a ton of things to do, after all, she had a kingdom to run. Despite what the people said by calling her the Evil Queen, she had never let us fall on hard times. She took care of her people, although they did not love her.

I was finished in about twenty minutes and knelt on the stool. Within ten minutes of situating myself, the door opened above me and I could hear my Queen descend. She walked over to the bed and sat at the end facing me.

“Let’s continue, shall we? I will use any and all the instruments I have in this room and we will find out what you like and don’t like. What you don’t like, I will take note of and we probably won’t do that again. I believe that’s called a hard limit. Have you thought of a safe word?”

I had thought of it briefly while I was bathing, but hadn’t settled on anything yet. “I have thought about it, Mistress, but I haven’t settled. Can you give me a few minutes to think?”

She nodded briefly and sat quietly. I closed my eyes, so I wasn’t distracted by her beauty. Even so, I knew she was watching me and I couldn’t think straight. I opened my eyes and asked, “May I use colors?” She considered briefly and nodded. “I could use green when I like something, red when I can’t handle it anymore and maybe yellow can mean to slow down or I need to check in with you, like to communicate with you.”

“You know, you’re good at this. We could have some real fun together.” I smiled at her and felt excitement course through my veins. She genuinely smiled back at me and I felt at peace. “You have a beautiful smile.”

“Thank you, Mistress, so do you.” Her smile fell and she set her face. I was sorry that I had said anything. I wanted to know what took her happiness away that she felt she couldn’t even smile. I brought my mind around to something that had me curious all night and braced myself to ask a question. “May I ask a question, Mistress?” She nodded. “Where did you get these toys and the idea for a playroom?”

A grim smile replaced her blank face as she considered her words. “Several years ago, I was traveling and I came upon an open field. There in the field were gypsies having an orgy. I stopped and walked through and saw many different things going on. A young gentleman stopped me and asked if I wanted to join in. I declined for the moment as another couple was intriguing me. She was tied up and he was spanking her. I asked the young man what they were doing. He explained to me the fine points of pleasurable pain and what they were partaking of was called BDSM. He enticed me to try it, but I didn’t want to be tied up. A few spankings had me going and it was the best orgasm I had ever had. Before I left the area, I bought several of their toys and created this space to hold them, so not everyone knows about my fetish. I’m still in touch with that young gentleman. He will bring me a new toy and show me how it works, although I very rarely let anyone give me pain.”

I thought he was one lucky man, but kept my face passive. She studied my indifferent face and took a breather. “I may let you spank my ass during sex sometime, but I will be the one handing out the pain in this room. Do you understand?”

“Yes, mistress,” I conceded. Then excitement coursed through my veins at possibly being able to spank the Queen. I would wait until she asked. She obviously had far more lovers than anyone knew. Oh well, I guess that was her business.

“Alright, so our lesson for today will be for you to hold it. You are not allowed to cum until I permit you.” I gulped. Would I be able to do this? “Follow me.”

I stood up from the stool and shook out my legs, walking over to the wall behind her. I looked at the chains and knew what she was about to do. “Stand facing the wall, now.”

I stood facing to the wall and watched over my shoulder as she took my left hand and attached a binder. She did the same with my other arm and both my legs. Her right hand was flung out and I watched as a wheel started to turn on its own; she had obviously enchanted it. I felt as my body suspended from the ground and I was raised about a foot off the ground.

“I’m going to warm you up first.” I felt a smack on my rear. She alternated between my cheeks and I counted about 20. She was right; there was pleasure in pain. My cock was as hard as rock.

The chains began to move again and soon I was settled on my feet again. She guided me over to the bed and had me lie on my back and bound my feet to the chains on the bed. She climbed on top of me and lowered herself over my cock until I was completely engulfed by her wet heat. She was breathing heavily and I felt her walls undulate around my cock. “Now remember,” she admonished, “no cumming until I say.”

She impaled herself over and over on my cock. Her delicious tightness felt so good squeezing my cock. She kneaded her hands over my abdomen. I felt the beads of sweat on my brow as I tried to clench my muscles to stop, but it felt like a loosing battle. “Please, mistress, I need to cum.”

She groaned and the mewling in her throat said she was close. She grunted out, “No.”

Her tummy tightened and her walls spasmed around me and she screamed through her high and still she impaled herself on me again and again. I pleaded, “Please, mistress, I can’t hold this much longer.”

She removed her hands from my stomach and started to play with her nipples as she bounced on my cock. I groaned and felt her walls spasm again and her scream as she completed her high. She was climbing higher this time, her body was shaking and trembling above me. Her whimpering and mewling told me this one was going to be her best one yet. I knew I couldn’t hold it anymore and that I was going to cum with her.

“Mistress,” I whimpered quietly, “I can’t hold it anymore.”

Of course, she couldn’t her me. The strain to hold my muscles was really getting unbearable. I really needed to work on this and strengthen those muscles. She reached out behind her and her hands found my thighs. Her breasts bounced in my face and I think my cock found that special spot inside her because she started to chant “Yes” as she climbed to her highest peak. Her tummy tightened and started to quiver. Her walls were seriously undulating over me and as she opened her throat, she let out her loudest scream yet, I splashed my seed inside her.

Her chest was heaving as she came down from her high and her hands settled on my stomach. Her eyes were closed as her breathing evened out from her three orgasms. She climbed off my now limp penis. She took the now flaccid member in her hands and I looked up into her eyes. She was angry.

Her tone was firm as she said, “I have not given you permission to cum yet.”

I humbled myself and apologised, “I’m sorry, mistress. I’m still new at this. I tried, I really did.”

Her eyes closed momentarily again and when she opened them, she looked completely calm. “I know you’re new at this, but I still wasn’t done with you. Because I hadn’t allowed you to cum, you have to be punished.”

She released the bonds, went to the shelf to choose her paddle and sat down at the foot of the bed. “Come here and bend yourself over my lap.”

I moved slowly to her lap and lay myself over. “You’re going to count for me, to 30 now.”

I gulped, that sounded high to me. I felt the sting on my rear end and counted, “One,” a sting on my other buttock, “Two,” she kept going higher, “12, 13,”. I clenched my butt and she struck my left buttock harder, it left me gasping, “17.” She kept the weight of the strikes that hard after that, “18, 19, 20.” After each count, I sniffed, my butt was on fire. For being a woman, she was strong and I was sure I wasn’t going to be able to sit for awhile. I finished the count, “28, 29, 30.”

My eyes glistened with unshed tears. Anymore strikes, I’m sure I would have been crying. Her eyes took on a kindly look as she sat me up and I winced. Her lips pursed at my cringe and she instructed, “You may lay down on the bed, Ainsley, and rest. I will bring your dinner to you later, but that is it for your lesson today.”

I moved to the head of the bed and lay on my side. She stood for a moment and then I felt her hand caress my cheek and then run through my hair. I turned my head to catch her eye and her eyes glistened as well. We held the gaze for about a minute and then she made her way to the stairs and the door. As the door closed behind her, the lights went out again.

The chains groaned in the corner and sweat coated my body. There were several creaks and taps. I felt as the tears rolled from my eyes. Was I ever going to get used to this? Darkness was my least favourite thing in the world. If I ever joined the rest of the guards, I would take my secret with me to the grave.

**Notes for the Chapter:**

> So, what do you think? Is that up to par in a BDSM scenario? Anything I need to work on? Let me know in the comments. Thanks. Hope you enjoyed!


	3. Day 2

**Summary for the Chapter:**

> Ainsley's third day and he experiences yet another pleasure of sex. Enjoy!

**Notes for the Chapter:**

> I started this in omniscience perspective and then remembered that it was supposed to be first person, so I switched it. If there are any problems, let me know, although I did edit it thoroughly. Looking foreword to seeing what you think. Please read and review.

**Chapter 3 Day 2**

The door opened the following morning and I quickly used the chamber pot and then situated myself on the stool at the bottom of the stairs. I could hear my Queen slowly make her way down the stairs in the utter blackness. Suddenly light appeared all around me. I blinked as my eyes adjusted from darkness to light. A finger trailed around from the center of my back over my right shoulder and trailed over my chest and up to tip my chin up.

My eyes trailed over her body as she came into my vision. She was wearing the same costume as yesterday, but a different corset. This one had a hundred little gems over the front of it and it glittered in the light.

Once the Queen was sure that she had my full attention, she said while she ran her hands over her body, “Today we are going to try a couple new toys. I was disappointed in you yesterday. Even though this is new to you, I expected you to try to be stronger. So today, we are going to work on endurance. I want you to remember that the same muscle you use to hold your pee is the same muscle you use to hold it, so you don’t cum so easily.”

I couldn’t take my eyes off the sensuality of my Queen. Even with all the leather she was wearing, I could tell she was really enjoying touching herself. She was so beautiful and my cock was at full attention. Queen Regina leaned forward to capture my lips while she ran her fingers through her wet slit. I gasped. She grabbed my cock and was massaging it with her fingers. Then while our mouths were engaged duelling, I felt something cold slide over the tip of my penis and down my shaft. She fit a strap over my balls, close to my body and then she pulled it through a loop drawing it tighter. The pressure built in my cock and I knew I wasn’t going to get any relief any time soon.

The lovely brunette pulled away from me and I looked down between my legs. There was a leather strap at the base of my cock and I knew this was supposed to help me learn how to hold it. I whimpered slightly.

She smiled at me and commanded, “Go stand against the wall.”

I stood and did as I was told and once again she chained me to the wall. Today she didn’t raise me from the ground, but instead proceeded to use her cat o’nine tails on me as is. I grunted and groaned from the strain as my cock throbbed as she lightly whipped me. While still in the binders, I felt as oil trailed down between my butt cheeks and down around my back door. What was she going to do?

I heard a loud sucking and wondered what she was sucking at? Her hand slid down between my cheeks and I felt as an object was placed against the skin of my hole. I clenched unknowingly and felt a slap against my left buttock.

“Don’t clench. Just relax.” Taking some slow deep breaths, I finally felt as my body relaxed. I grunted as she pushed the object through past my sphincter. Pleasure coursed through my anus and I whimpered as the object pressed against my prostate. Finally, she released the binders, commanding, “Go lie on the bed and I will be with you momentarily. Don’t touch anything I’ve put on or in you.”

Carefully, moving slowly, I walked over to the bed. I sat briefly and ahhhed with the increasing pressure in my anal canal. Quickly, I laid myself down, trying to relieve some of the pleasurable pressure in my backside. I closed my eyes and my head lolled with all my nerve endings screaming at me in excitement. I forgot all about my throbbing cock with the pleasure I was receiving in my butt. Maybe she would use some of those phallic objects on me. I thought I might actually enjoy it. 

She bound my wrists and ankles again and slowly slid herself on my extended cock. She sat momentarily watching the pleasure on my face from the ball she had pressed against my prostate. Then she started to move and I cried out in bliss as the ball began to massage against that area. She bounced on my cock, rolling her hips against mine. My mind was gone with all the delight I was experiencing, and the Queen played with her own nipples, allowing her fingers to graze her skin as she rode me.

She rode me for a long time, feeling how her walls enveloped my member and squeezed me every once in a while. Her senses were heightened and without even touching her clit, she felt herself climb higher and higher. Loving the sounds of our skin slapping against each other and watching me enjoy my toy, she reached her pinnacle and fell over, opening her mouth to scream through her high.

I was still hard and she smiled as she knew I would stay that way until she let me cum. She continued to ride me as she came down from her orgasm and then she pitched forward and my tip touched her sweet spot and she started climbing again. She placed her hands on my chest and slid her body over my member, undulating each time it hit her g-spot.

I was in heaven. There was a wonderful warmth spreading through my anal canal and there was a fullness. I wondered if women felt this way, if she felt this way, with my cock in her. As delightful as the prostate pleasure was, her riding my cock was taking away from the full sensation of just the bliss against my prostate. But I wouldn’t take this back for the world.

My eyes were slit open and I watched as she rode my cock through from one orgasm after another. Once she was a quivering mess from three orgasms, she pulled herself off my cock and sat down next to me breathing heavily.

Once she felt a little less shaky, she turned and removed the binders from my limbs. She snapped her fingers and chains fell from the ceiling above the bed. “Hold on to the bar. Now.”

I slowly moved from my position and felt a slap across my left buttock again. “Move faster.”

I huffed as I went to grasp the handle. Hopefully she wouldn’t see this as insubordination. She shook her head at me, “My fault, face the other way.”

I turned to face the head of the bed and reached for the bar. She slipped the binders over my wrists and bound my ankles again. She reached between my cheeks again and I felt as she pulled a chain and the ball was pulled free of my back door. I gasped, flexing my muscles back there, huffing as the still sensitive nerves reminded me of the pleasure I had received. She dangled the ball in my face and my brows rose.

“From that little ball,” I whispered. The Queen chuckled. She unbuckled the leather over my balls and cock. Again, I gasped as the pressure released slightly, but my member still throbbed from the heightened sensations of needing to cum.

The Queen situated herself on her hands and knees in front of me, sliding down to let her elbows settle on the bed under her. Her butt was high in the air and, if I wasn’t bound to the bar above the bed, I would have liked to touch everything I saw. She was so wet from the orgasms she had already had and her pussy glistened in the light.

She looked over her shoulder at me as she gave me the next set of commands, “Obviously, you may not touch, but you can watch. The bars above the bed will allow you to thrust forward, but I will set the pace. Make sure you don’t cum until I tell you.”

I watched how her chocolate eyes took on a golden glint in the light and my breathing was shallow as I looked at the beautiful body of my Queen. Her skin was so smooth and the light played with each bead of sweat that rolled over her body. The scent of her cum laden body filled my nostrils and they flared. My chest thrust forward as happiness filled my being. I didn’t care in that moment that I was being used for the Queen’s pleasure for she was giving me pleasure as well.

As I pushed forward to sink into her tight walls, she rocked back taking me inside her. She groaned as my member massaged over her sweet spot again. I was pretty sure she was not disappointed in this position and would probably remember it for future sessions. We found a rhythm together. I concentrated on that little muscle to stop my orgasm from taking over. I thrust into her body over and over. She rocked backwards and forewords; her moans and mewls rising in pitch. She looked over her shoulder at me again. What was she thinking? Was I doing well? Would she find new reasons to punish me? Maybe she would tease me more.

She looked so sexy watching me in my concentration. Could she not tell that my eyes were slightly open and I could see how sexy she really was? I closed my eyes fully as my cock pulsed. I needed to cum, but she hadn’t given me permission yet. I huffed and groaned as I sunk within her tight walls again. Her head was thrown back and her neck glistened in the light. Her curls flowed over the arch of her back. I felt as her walls tightened and undulated, and then her body quivered. I knew she was reaching a new high. Her throat opened and she screamed, “Ainsley, now!”

A couple more pumps and my seed poured into her, spurt after spurt, as we tumbled through our high together. I felt her juices splash over my balls and the scent filled my senses. I gloried in her achievement and smiled as she collapsed beneath me. She rolled over onto her back and caught my gaze as I delighted in her beauty.

Her breath caught. I was just her night guard, she wasn’t falling for me, was she? Her eyes closed to slits, and I thought she must have been reminiscing again. Did I remind her of someone from her past? Was she delighting in their union once again in her imagination?

Flicking her wrist towards the corner, she filled the tub with hot water. “I’ll leave you and send you your meal. Feel free to clean up.”

I made my way towards the tub, slipping into the hot water to clean up after that delicious sex. My belly gurgled its discontent and I anticipated the meal to come. As I moved to sit on the bed, a tray appeared before me and I indulged in the breakfast before me. Once finished, I turned to the bed. I was exhausted and fell into a deep sleep once my head hit the pillow. I didn’t notice as I was plunged, once again, into darkness.


End file.
